Kanamycin produced by Streptomyces kanamyceticus is a 4,6-disubstituted 2-deoxystreptamine-containing aminoglycoside antibiotic as are gentamicins and tobramycin, whereas neomycins and butirosins are 4,5-disubstituted aminoglycosides.
These types of antibiotics are produced mainly by actinomycetes and have been widely used for a long time. Like other antibiotics, the appearance of aminoglycoside-resistant bacteria, which produce aminoglycoside-modifying enzymes, cause serious problems. The issue of resistance has been addressed by the semi-synthetic variants of naturally-occurring aminoglycosides such as amikacin, dibekacin, and arbekacin. The central 2-deoxystreptamine (2-DOS) and pseudodisaccharides 2′-N-acetylparomamine, paromamine, and neamine are common biosynthetic intermediates of most aminoglycosides. The biosynthetic route to neamine via 2-deoxystreptamine and paromamine was elucidated using recombinant enzymes involved in butiroin and neomycin biosynthesis.